Phenethylamine → alpha-[(Phenethylcarbamoyl)methyl]cinnamic acid

HRID 1655746Notes

Reaction equation

HRID 1655746 reaction equation
[CH:1](=[C:8]1[CH2:13][C:12](=[O:14])[O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][NH2:23])=[CH:17][CH:16]=1>C(Cl)Cl>[CH2:22]([NH:23][C:12]([CH2:13][C:8](=[CH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]([OH:11])=[O:10])=[O:14])[CH2:21][C:18]1[CH:19]=[CH:20][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 1001PhenethylamineHCID 222996Phenylitaconic anhydride

Product 1

HCID 54394250alpha-[(Phenethylcarbamoyl)methyl]cinnamic acidYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

226 mg (1.2 mmol) of benzalsuccinic acid anhydride were treated in 20 ml of methylene chloride with 0.15 ml of 2-phenethylamine and subsequently stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel, to obtain 260 mg (70%) of α-[(phenethylcarbamoyl)methyl]cinnamic acid, MS: 309 (M)+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-c9ce86940efa48f98dcf91f9845cffae
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

Loading…